Ethyl (2-((2-hydroxypropyl)amino)-2-oxoacetyl)glycinate → Ethyl (2-oxo-2-((2-oxopropyl)amino)acetyl)glycinate

HRID 1016258

Reaktionsgleichung

Reaktionsgleichung von HRID 1016258
[CH2:1]([O:3][C:4]([CH2:6][NH:7][C:8]([C:10]([NH:12][CH2:13][CH:14]([OH:16])[CH3:15])=[O:11])=[O:9])=[O:5])[CH3:2].Br([O-])(=O)=O.[Na+]>O.C(OCC)(=O)C.[Cl-].[Na+].O.O.[Ru](Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([CH2:6][NH:7][C:8]([C:10]([NH:12][CH2:13][C:14](=[O:16])[CH3:15])=[O:11])=[O:9])=[O:5])[CH3:2]

Komponenten

7

Edukt 2

HCID 10537524Ethyl (2-((2-hydroxypropyl)amino)-2-oxoacetyl)glycinateHCID 23668195Sodium Bromate

Produkt 1

HCID 10823329Ethyl (2-oxo-2-((2-oxopropyl)amino)acetyl)glycinateAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 6093376Ruthenium trichloride hydrateKatalysatorHCID 962WaterLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

To a stirred solution of N-(ethoxycarbonyl-methyl)-N′-(2-hydroxy-1-propyl)oxamide (8.0 g, 34.5 mmol), as prepared in the preceding step, in water (50 mL) under nitrogen at 50° C. was added ruthenium (III) chloride hydrate (75 mg, 0.35 mmol). The reaction flask was removed from the heating bath, and a solution of sodium bromate (5.2 g, 34.5 mmol) in water (40 mL) was added dropwise. The reaction mixture was allowed to cool to room temperature, and then diluted with ethyl acetate and brine. The aqueous layer was extracted with ethyl acetate (2×), then saturated with sodium chloride and extracted again (×2). The combined ethyl acetate layers were washed with brine, dried over Na2SO4, and treated with activated carbon. Evaporation of the solvent and drying under high vacuum provided the title compound as a white solid (7.3 g, 92%). 1H NMR (400 MHz, CDCl3) δ 7.99 (s(br), 1H), 7.84 (s(br), 1H), 4.24 (q, 2H, J=7.1 Hz), 4.19 (d, 2H, J=5.2 Hz), 4.10 (d, 2H, J=5.7 Hz), 2.24 (s, 3H), 1.30 (t, 3H, J=7.1 Hz).

Aufarbeitung

  1. customThe reaction flask was removed from the heating bath
  2. extractionThe aqueous layer was extracted with ethyl acetate (2×)
  3. extractionsaturated with sodium chloride and extracted again (×2)
  4. washThe combined ethyl acetate layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. additiontreated with activated carbon
  7. customEvaporation of the solvent
  8. customdrying under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-05a75e7048db4cf9b4b258b7cef0d25f
Quelldatensatz
uspto-grants-2002_11
Patentnummer
US06476016B2

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